Author: Jessica.F

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C22H19N3O6

210.7 g (0.5 mol) of (S)-2-{[2-oxo-3-(4-(3-oxomorpholine)phenyl]oxazolidine-5-yl] prepared in Example 7 was added to the reaction flask. Methyl isonon-1,3-dione (formula VII), 1500 ml of anhydrous ethanol, and 500 ml of a 30% aqueous solution of methylamine were stirred well and heated to 40 C. to 60 C. for 8 hours. TLC control (2) Chloroethane:methanol = 20:1, volume ratio) The reaction is complete. Adjust the pH to between 1-2 with 10% hydrochloric acid, precipitate a large amount of white solid, cool down to about 15C, stir for 2 hours, filter and filter cake with 300ml The mixture was washed with anhydrous ethanol and dried under reduced pressure to obtain 147.0 g of a white solid (the compound of Formula VIII) in a molar yield of 89.7%. The HPLC purity was 98.7%.

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University Fangzheng Group Co., Ltd.; Peking University Pharmaceutical Co., Ltd.; Peking University Medical Treatment Industrial Group Co., Ltd.; Xu Hong; Li Linfeng; Zhang Zheng; Wang Wei; Ren Juan; (18 pag.)CN105085507; (2017); B;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 56341-37-8, name is 6-Chlorooxindole, A new synthetic method of this compound is introduced below., Safety of 6-Chlorooxindole

A mixture of 750 ml of dichloromethane, 150 g of 6-chlorooxindole, 161.6 g of chloroacetyl chloride and 477.2 g of aluminium chloride was refluxed for 9.5 hours. The reaction mass was quenched into a mixture of crushed ice and 135 ml of hydrochloric acid. The formed solid was filtered, and the wet compound was washed with water. The wet compound was dissolved in 3525 ml acetic acid by heating to 70 to 80 C., then carbon was added and the mixture was stirred briefly at the same temperature, and the carbon was removed by filtration and washed with 15 ml of acetic acid. The filtrate was allowed to cool to about 20 C. for solid formation. The solidd was filtered, washed three times with 600 ml of water, and then dried to yield 148.5 g of the title compound.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Venkataraman, Sundaram; Rao, Uppala Venkata Bhaskara; Muvva, Venkateswarlu; Chitta, Vijayawardhan; US2006/89502; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 552330-86-6, name is 5-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 552330-86-6, COA of Formula: C8H6BrNO

Step 1: 5-(Methylthio)isoindolin-1-one (0509) (0510) 5-Bromoisoindolin-1-one (15 g, 70.74 mmol) and sodium methyl mercaptide (12.40 g, 176.85 mmol) were mixed together in DMF (150 mL) and heated to 100 C. for 1 h. The reaction mixture was cooled to room temperature and poured into water (160 mL). The product extracted with EtOAc (400 mL). The layers were then separated and the aqueous was extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine (3×100 mL). The organic extracts were combined, dried using a phase separator cartridge and concentrated in vacuo. 5-(Methylthio)isoindolin-1-one (12.00 g, 95%) was obtained as a yellow solid. The material was used in the next step without further purification. (0511) LC/MS: m/z=180 [M-H]-. 1H NMR (500 MHz, DMSO-d6) delta 2.54 (s, 3H), 4.33 (s, 2H), 7.33 (d, 1H), 7.44 (s, 1H), 7.56 (d, 1H), 8.43 (s, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Synthetic Route of 1074-82-4,Some common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, molecular formula is C8H4KNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 mm at room temperature. After complete addition, the reaction mixture was stirred at 90C for 1 8 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered anad concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65% yield).H NMR (400 MHz, CDCI3): d 7.82 (dd,J= 5.5, 3.1 Hz, 2H), 7.69 (dd,J= 5.5, 3.0 Hz, 2H),3.68 (t, J= 7.2 Hz, 2H), 3..38 (t, J= 6.8 i-iz, 2Ff). 1.93-1.85 (n:i, 2H), 1.70 (p, J= 7,5 Hz, 2H),1.53-1.43 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Potassium 1,3-dioxoisoindolin-2-ide, its application will become more common.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; SHIRUDE, Pravin S.; (258 pag.)WO2017/6282; (2017); A1;,
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These common heterocyclic compound, 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 5-Bromo-2-methylisoindolin-1-one

General procedure: 5-Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solutionof 2 M Na2CO3 (3 mL) and Pd(dppf)Cl2 (94 mg, 0.12 mmol) were added and the entiremixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30mmol) was added and reflux continued under N2 overnight. Upon cooling, the mixture wasdiluted with water (100 mL) and extracted with CH2Cl2 (6×50 mL). The combined organicfractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure togive a crude solid which was purified by flash column chromatography on silica gel (EtOAcas eluant). The title compound was isolated as a light-brown solid (510 mg, 97percent).

The synthetic route of 5-Bromo-2-methylisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
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Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 675109-26-9

A mixture of 6-bromoisoindolin-1-one (287 mg, 1.35 mmol), 1-methyl-5-(tributylstannyl)-1H-imidazole (500 mg, 1.35 mmol), Pd(dppf)Cl2 (33 mg, 0.041 mmol) and Cs2CO3 (1.32 g, 4.05 mmol) in dioxane (50 mL) and water (8 mL) was heated to 100 C. overnight. After cooling, the mixture was concentrated under vacuum and purified by column chromatography on silica gel ((1%-3% MeOH in DCM) to afford 9A (220 mg, 76% yield) as a brown solid: 1H NMR (400 MHz, DMSO-d6) delta 8.66 (s, 1H), 7.76-7.15 (m, 4H), 7.15 (s, 1H), 4.43 (s, 2H), 3.72 (s, 3H); ESI m/z 214.1 [M+1]+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 13220-46-7, A common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, molecular formula is C9H9NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

5-Chloro-4-methyl-2-oxindole A suspension of 3.0 g of 4-methyl-2-oxindole was stirred in 50 mL of acetonitrile at room temperature while 3.3 g of N-chlorosuccinimide was added in portions. Trifluoroacetic acid (1 mL) was then added. The suspension was stirred at room temperature for 3 days during which time solid was always present. The white solid was collected by vacuum filtration, washed with a small amount of cold acetone and dried overnight in a vacuum oven at 40 C. to give 2.5 g (68%) of 5-chloro-4-methyl-2-oxindole.

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5428-09-1, name is 2-Allylisoindoline-1,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5428-09-1, Safety of 2-Allylisoindoline-1,3-dione

General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3×20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang; Tetrahedron; vol. 68; 24; (2012); p. 4919 – 4926;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Formula: C8H8N2O2

1-{1-[6-(5-nitro-2,3-dihydro-indole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 150 mg (0.47 mmol) TBTU were added to 150 mg (0.44 mmol) 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 75 mg (0.46 mmol) 5-nitro-2,3-dihydro-1H-indole, 100 muL and (0.712 mmol) triethylamine in 1.5 mL DMF and the mixture was stirred overnight at RT. The reaction mixture was poured onto 30 mL water. The precipitated product was suction filtered and dried at 50 C. in the CAD. Yield: 130 mg (61% of theoretical) ESI-MS: m/z=487 (M+H)+

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 41663-84-7, name is 2-Methyl-5-nitroisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6N2O4

Example 12Conversion of Treated 4NPI to BisimideA 2-liter, 5-necked oil jacketed glass vessel, equipped with a Dean and Stark receiver topped with a reflux condenser, a mechanical stirrer, and means for maintaining a nitrogen atmosphere, was charged with 335 g (1.63 mol) of 4-NPI in 1000 g of toluene (resulting from the bicarbonate treatment of the 4NPI/water slurry, see above), and 6.2 g (0.008 mol HEG-Cl) of a catalyst solution composed of 34.4% by wt. HEG-Cl, 10.0% sodium chloride, and 55.6% water. An additional 500 g of toluene was added. The solution was brought to reflux using an external hot oil unit set at 120 C. to supply hot oil to the jacket of the vessel, and the water was removed by azeotropic distillation. Approximately 500 g of toluene was removed during the distillation. The dry 4-NPI/catalyst toluene solution was then added via a flexible fitting to a 5-liter, 5-necked oil jacketed glass vessel (equipped with a Dean and Stark Receiver topped with a reflux condenser, mechanical stirrer, and means for maintaining a nitrogen atmosphere) containing 222 g (8.15 mol) of BPA disodium salt and 700 g of toluene (the salt solution can also be added to the NPI solution). The temperature on the 5-liter vessel was maintained at 120 C. using a hot oil recirculating unit. HPLC of the reaction mixture indicated that the displacement reaction was complete in 60 min. to afford a 99.4% yield of BPA bisimide. The mixture was cooled to 80 C. and extractively purified with three 580 mL portions of 1% aqueous sodium hydroxide to afford pure bisimide with a yellowness index (YI) of 2.0.The YI was measured with a Macbeth 7000 spectrometer using ASTM D-1925. A blank of methylene chloride was measured for YI prior to measurement of the sample. This YIblank measurement was recorded for use in correcting the final measurement. About 0.5 g of a sample was dissolved into 10 mL of methylene chloride. The sample was then filtered through a 0.5 g HPLC filter. The mixture was then transferred to a 3.7 cm×5 cm×10 mm path length cell. The cell was placed into the calorimeter (ASTM D11925) and the YI was determined.The equation (I) below was used to correct the YI. This equation (I) is general and allows for solutions to also be measured for YI.YIcor=(YImeas-YIblank)*0.5*100/(wt. Sample in G*% solids of the sample) (I) The washes were done at 80 C., with a 5 minute agitation time and a 7 minute settling time. The YI of the material was 2.2. The YI of a typical reaction (without bicarbonate treatment of the 4NPI/water slurry) is 3 to 4.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SABIC Innovative Plastics IP B.V.; US2009/292128; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem